The 2019 sailing documentary Maiden received rave reviews as a human-interest story that featured excellent racing footage and the heartfelt recollections of an all-female team led by then 25-year-old Briton Tracy Edwards. During the 1989-90 Whitbread Round the World race, Edwards and the crew of Maiden broke into the male-dominated enclave of professional offshore sailing, won two legs and proved the doubters wrong by showing that women could compete at the highest level of the sport.

The story of Maiden also includes the only American onboard, Dawn Riley. In 1989, Riley was a young Detroit, Michigan, native working as a boat captain when she joined the Maiden crew. She went on to lead a team in the 1993-94 Whitbread, participate in four America’s Cup campaigns and is now CEO of Oakcliff Sailing in Oyster Bay, New York (oakcliffsailing.org). Laurie Fullerton spoke to her.

When you joined Maiden in 1989, you were 25-years-old. Would you say you were one of the most experienced women coming into the 1988-89 Whitbread Round the World Race?

I had sailed long distances with my family, which is how it began for me, and by the time I was 18, I was a boat captain and engineer. I had not been a college sailor, but instead, I worked as a boat captain in order to pay for college. This led me to do boat deliveries in the Southern Ocean Racing Circuit (SORC). So, by the time I came to sail on Maiden, I had been in the sailing industry for 10 years.

What was yacht racing like at a professional level at the beginning of your career?

It is true as it is described in the film that in large part the doors to professional women sailors at this level were completely closed. For me, in the United States, I guess I was good enough to be at the top of the sport for my age. I had opportunities in sailing and sailmaking, but that didn’t mean I didn’t face pretty much blatant sexual harassment in the trade. It just didn’t stop me.

The film depicts male resistance to women being anything more than cooks in the Whitbread Race prior to 1989. Did you ever consider coming up through the ranks as a cook as Edwards did?

No way. I was a captain and an engineer already. Still, there were many times when I tried to get on an offshore professional racing boat in the United States and I was told that the team “didn’t need any (expletive deleted) women on their boat.”

What was the reaction you received from your male contemporaries when you told them you were going to do the Whitbread?

One of the first things a man said to me when I told him I was going to do the Whitbread was, “Bring warm socks.” I think the overall reaction from my male contemporaries in the United States was that they were not impressed. At that time, there were very few Americans in the Whitbread, and till then we had not had a stopover in the U. S.

When I made the team, I was a sailmaker and dealing with things at work. For example, at the loft, they set up a pink “D” (for Dawn) on the wall, and they used to use it as a dartboard.

I was also working as a boat captain, and my boss told me, “Don’t do it. It is just escaping from the real world.” Interestingly, I was able to demand at least a 100 percent pay raise from boat owners when I returned.

The film suggests that you played a key role with the tactics. The team also won two of the most difficult legs of the event. What was it actually like out there?

The place where I was ahead of the others in knowledge and experience was with the boat mechanics, sail trim and speed. One has to remember that back then you couldn’t call anyone or have a conversation about anything that was going wrong. Whatever we repaired or did on the boat, we had no outside help. Everybody had their own jobs and area of expertise. I didn’t know anything about plumbing and didn’t want to know. In the film, the team’s doctor says she would handle the plumbing as she had the most experience with it! I loved that line.

Based on the onshore interviews featured in the film, many journalists during the first legs were unclear about what to ask the women. What are some examples?

I remember being in Punta del Este in Uruguay after finishing the first leg. We were on the dock and the men were being asked a lot of in-depth questions. I remember we would get questions like, “Is it a nice thing that you arrived today and not yesterday because the sun came out today?”

Also, immediately after the race ended, I was invited by myself to appear on the David Letterman show. I will never forget that because the first thing they did was show the clip of all of us in our bathing suits as we sailed into Florida. I had been really against the idea of wearing bathing suits as we sailed into Florida in the first place. I think it turned out to be a huge story or publicity stunt, but I wish we hadn’t done it. I was on Letterman and there was a photo of me leaning over and grinding the jib wearing my swimsuit on a huge screen above Letterman’s head. On national television, Letterman turned to me and said, “Wow, have a look at them winches!” I believe he was referring to something else in the picture. It was really embarrassing.

Many film reviews (non-sailors and sailors alike) praise the movie and many mention that they wonder what the people on the team did next. Did your time on Maiden prove to be a turning point in your career?

People kind of assume the race on Maiden was a turning point or launching point. It definitely helped my career, but it wasn’t a game-changer, more of an accelerant. Ironically, when I came back everyone thought I was an offshore sailor, and I had trouble getting rides on round-the-buoys boats—until I did the America’s Cup.

Near the end of the film, the veteran British journalist Bob Fisher proudly states, “By the time the women finished the Whitbread Round the World Race they were heroes. They were not heroines, but heroes, because by that time they really had become men.” Do you think the sport of sailing still faces this kind of double standard?

I think in a lot of ways sexism has hurt our sport. When you look at it from a marketing perspective, half of the possible participants in this sport are left out of it at the highest professional level, and with so little diversity you dwindle away half of your fans, or half of your audience.

So, would you say that the sport of sailing remains male-dominated?

Yes, there are more men than women on most racecourses, but that is often not the case at Oakcliff. To effect this type of change in other areas, we need women in power, decision makers, owners, tacticians, project managers, skippers, and then the gender bias will slide away, naturally and quite quickly.

You went on to skipper a boat in the 1990-91 Whitbread Round the World Race, participated in or managed four America’s Cup campaigns, and you are now the CEO at the renowned Oakcliff Sailing center in New York. Are you satisfied with your career?

After my fourth America’s Cup, I was looking at writing another book and doing more consulting, racing superyachts and even running for Congress. Then I was hired as a consultant and designed what was to become Oakcliff Sailing. I meant to stay for three years to get it up and running, but it has now been 10 years, and I don’t see myself going anywhere soon. It is too exciting to see the changes we are able to make in young lives. I am proud of every level of our programs, but I believe our offshore sailing program is arguably one of the strongest in the country.

What has been your favorite part about the release of this film?

It is a good film, and I have experienced three responses from people. One is that people mention they had forgotten all about it. The other is that people didn’t know this epic event had happened. And the coolest thing is the reaction from young people who see it and get really stoked about it. That is my favorite part. 

March 2020